More storm clouds blew into Arsenal’s season on Thursday when they were given
a nightmare of a draw in the Champions League and also heard the dispiriting
medical bulletin that their in-form attacker Lukas Podolski was out for up
to 10 weeks.

The one silver lining to the dark clouds was the arrival of a free agent and old boy Mathieu Flamini. Hardly the cavalry, though.

These are tense times for Arsenal, and particularly their manager, Arsène Wenger. They should have been celebrating qualifying for the group stages but the play-off victory over Fenerbahce cost them Podolski with an injured hamstring, further depleting their resources.

The club, correctly, have offloaded much dead wood this summer but have not brought in replacements.

Arsenal’s board point out the club have major sums to invest in players in transfer fees and wages but they cannot nail down deals. Ivan Gazidis, the club’s chief executive, was his usual polite self here in Monaco on Thursday but is clearly frustrated by the failure to bring in players.

When the smoke clears through this transfer window, a discussion will need to take place between board and Wenger, who has been criticised by fans of dithering in the market.

He cannot be blamed for a brutal draw though. The sun shone in Monaco and the draw burned Arsenal. Wenger’s side were amongst the eight top seeds but were given little joy when pitted against Marseille, whose intimidating Stade Velodrome ground is never an easy trip.

Pot Three gave Arsenal the worst possibility, a meeting with last season’s finalists Borussia Dortmund, who have managed to retain for one more season the formidable attacking services of Robert Lewandowski.

Hoping for some respite from Pot Four, Arsenal were presented with another firecracker, this time in the shape of Napoli. The Italians are coached by the wily Rafael Benítez, who has spoken frequently of his admiration for Wenger but will relish the chance to prove a point to an English audience.

Napoli’s attack will be led by Gonzalo Higuain, a painful reminder of Wenger’s failure to close transfer deals. Arsenal were linked with Higuain but became distracted by the possibility of landing Luis Suarez and ended up with neither.

Napoli’s quality, and particularly that of their young playmaker Lorenzo Insigne, was seen in the 2-2 draw with Arsenal in the pre-season Emirates Cup.

Arsenal are working hard to bring in new signings but so far have only the France Under-21 forward Yaya Sanogo and free agent and old boy Mathieu Flamini. “The best years are in front of him now – the next three years,’’ Wenger told the Arsenal website. “Physically, he is perfect.

He was tested, prepared and he is physically in fantastic shape.

“He knows how we play football, knows the club and had a huge desire to come back. He was available because he was out of contract and he is a quality player, and a focused player, so those were all the reasons that pushed me to make that decision.”

Arsenal are still interested in Yohan Cabaye but will need to improve their £10 million offer substantially to make Newcastle United think about the possibility of selling one of their most important players.

Cabaye could also go to Paris St-Germain. Arsenal have also been linked with three Real Madrid players, Karim Benzema, Mesut Ozil and Angel Di Maria, but none has shown much interest in Arsenal. Chelsea are emphatic that Juan Mata, whose father was a guest of Arsenal the other night, “will not be leaving”.

Others Arsenal have been linked with include the Juventus forward Fabio Quagliarella and the St-Etienne midfielder Josuha Guilavogui.

As it stands, they will have a very inexperienced bench when Spurs visit the Emirates on Sunday. In recent years, Arsenal have reacted strongly to the “mind the gap” cries in north London but the contrast with Spurs bench will be considerable. Andre Villas-Boas has bought well this summer, using the imminent Gareth Bale money judiciously.

“When you think that we lost three players of the stature of [Mikel] Arteta, [Alex] Oxlade-Chamberlain and Podolski for three months basically before the season really starts, it’s very hard to take. We are in a position where you want some more players," said Wenger.

Aaron Ramsey (groin) and Jack Wilshere (ankle) “will be involved” against Spurs, according to Wenger, who hopes to have Thomas Vermaelen back after the international break.